WO2018031373A1 - Polyol acrylé et acylé ou acétalisé en tant que substitut d'origine biologique pour matériaux durs, rigides, thermoplastiques et thermodurcissables - Google Patents

Polyol acrylé et acylé ou acétalisé en tant que substitut d'origine biologique pour matériaux durs, rigides, thermoplastiques et thermodurcissables Download PDF

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Publication number
WO2018031373A1
WO2018031373A1 PCT/US2017/045340 US2017045340W WO2018031373A1 WO 2018031373 A1 WO2018031373 A1 WO 2018031373A1 US 2017045340 W US2017045340 W US 2017045340W WO 2018031373 A1 WO2018031373 A1 WO 2018031373A1
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WO
WIPO (PCT)
Prior art keywords
polyol
copolymer
monomer
acrylated
average degree
Prior art date
Application number
PCT/US2017/045340
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English (en)
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WO2018031373A8 (fr
Inventor
Eric W. COCHRAN
Nacu HERNANDEZ
Michael Forrester
Original Assignee
Iowa State University Research Foundation, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Iowa State University Research Foundation, Inc. filed Critical Iowa State University Research Foundation, Inc.
Publication of WO2018031373A1 publication Critical patent/WO2018031373A1/fr
Publication of WO2018031373A8 publication Critical patent/WO2018031373A8/fr
Priority to US16/272,261 priority Critical patent/US11248076B2/en
Priority to US17/554,544 priority patent/US11813892B2/en
Priority to US18/468,464 priority patent/US20240001711A1/en

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
    • C04B26/02—Macromolecular compounds
    • C04B26/26—Bituminous materials, e.g. tar, pitch
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
    • C04B2111/0075—Uses not provided for elsewhere in C04B2111/00 for road construction
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/02—Alcohols; Phenols; Ethers
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/24—Macromolecular compounds
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2641—Polyacrylates; Polymethacrylates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2438/00—Living radical polymerisation
    • C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
    • C08F2500/01—High molecular weight, e.g. >800,000 Da.

Definitions

  • the glycerol molecule was successfully modified such that when it was polymerized soft thermoplastic elastomers were created. These soft thermoplastic elastomers can be used in a wide range of applications, i.e. pressure sensitive adhesives, viscosity modifiers, etc.
  • Another aspect of the present invention relates to a method for preparing a fracking liquid.
  • the method comprises mixing the thermoplastic homopolymer, the
  • the copolymer is a thermosetting copolymer.
  • the acrylated and acylated or acetalized polyol monomeric units have different degrees of acrylation and acylation or acetalization of hydroxyl groups.
  • the acrylated and acylated or acetalized polyol monomeric units have different degrees of acrylation and acylation or acetalization of hydroxyl groups.
  • the average degree of acylation in acrylated and acylated sorbitol can range from 0.001 to 5.9.
  • the average degree of acrylation in acrylated and acylated isosorbide can range from 0.001 to 2.
  • the average degree of acylation in acrylated and acylated isosorbide can range from 0.001 to 2.
  • the average degree of acrylation in acrylated and acylated dextrose can range from 0.001 to 4.9.
  • the average degree of acylation in acrylated and acylated dextrose can range from 0.001 to 4.9.
  • One or more acrylated and acylated or acetalized polyol monomeric units of the PA block can contain one or more alkoxy groups.
  • Exemplary methacrylamides include N-(2- aminoethyl)methacrylamide (hydrochloride) (AEMAm) and N-(3-aminopropyl)methacrylamide (hydrochloride) (APMAm), N-(2-(dimethylamino)ethyl)acrylamide (DEAPMAm), N-(3- (dimethylamino)propyl)methacrylamide (hydrochloride) (DMAPMAm), etc.
  • the stoichiometric ratio of the acrylic reagent to the polyol can range from 1 to the maximum number of the hydroxyl functionalities in the polyol molecule.
  • the stoichiometric ratio of the acrylic reagent to glycerol typically ranges from 1 to 3.
  • the method comprises providing an acrylated and acetalized polyol composition comprising plural polyol monomeric units.
  • the polyol monomelic units being acrylated and acetalized.
  • initiation is typically based on the reversible formation of growing radicals in a redox reaction between various transition metal compounds and an initiator.
  • GTR ground tire rubber
  • cryogenic GTR is produced by shredding the tire into relatively large pieces and then subjecting the rubber to grinding under cryogenic conditions; ambient or warm-ground GTR is produced under warm or ambient grinding procedure.
  • the shredding and pulling apart of the tire rubber at ambient temperatures produces irregular particles having a high surface area which desirably increases the number of reactive sites available for bonding or cross-linking with the acrylated polyol-based
  • thermoplastic copolymer a thermoplastic block copolymer, or a thermoplastic statistical copolymer as an asphalt additive, modifier, and/or filler, with a weight percentage in the range of 0.01 % to 1.05 %, into an asphalt composition to form a homogeneous asphalt composition.
  • the asphalt composition comprises i) an asphalt component, and ii) a crumb rubber having a weight percentage in the range of 1 % to 15 %. Any of the thermoplastic homopolymer, copolymer, block copolymer, or statistical copolymer discussed in the above embodiments can be used herein.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Ceramic Engineering (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un homopolymère, un copolymère, un copolymère séquencé et un copolymère statistique comprenant plusieurs motifs monomères de polyol. Les motifs monomères de polyol sont acrylés et acylés ou acétalisés. Les motifs monomères de polyol acrylés et acylés ou acétalisés présentent un degré moyen d'acrylation égal ou supérieur à 1, mais inférieur au nombre de groupes hydroxyle du polyol et ayant un degré moyen d'acylation ou d'acétalisation qui est égal ou supérieur à 1, mais inférieur au nombre des groupes hydroxyle du polyol. La présente invention concerne également un procédé de fabrication des homopolymères, copolymères, copolymères séquencés et copolymères statistiques, et leur utilisation dans diverses applications, comme les modificateurs de bitume-caoutchouc, les adhésifs, ou un additif dans un fluide de fracturation hydraulique destiné à la fracturation hydraulique pour le forage de puits de pétrole.
PCT/US2017/045340 2016-08-12 2017-08-03 Polyol acrylé et acylé ou acétalisé en tant que substitut d'origine biologique pour matériaux durs, rigides, thermoplastiques et thermodurcissables WO2018031373A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US16/272,261 US11248076B2 (en) 2016-08-12 2019-02-11 Acrylated and acylated or acetalized polyol as a biobased substitute for hard, rigid thermoplastic and thermoset materials
US17/554,544 US11813892B2 (en) 2016-08-12 2021-12-17 Acrylated and acylated or acetalized polyol as a biobased substitute for hard, rigid thermoplastic and thermoset materials
US18/468,464 US20240001711A1 (en) 2016-08-12 2023-09-15 Acrylated and acylated or acetalized polyol as a biobased substitute for hard, rigid thermoplastic and thermoset materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662374414P 2016-08-12 2016-08-12
US62/374,414 2016-08-12

Related Child Applications (1)

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US16/272,261 Continuation-In-Part US11248076B2 (en) 2016-08-12 2019-02-11 Acrylated and acylated or acetalized polyol as a biobased substitute for hard, rigid thermoplastic and thermoset materials

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WO2018031373A8 WO2018031373A8 (fr) 2018-04-19

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CN108707443A (zh) * 2018-05-18 2018-10-26 杭州海维特化工科技有限公司 一种柔强可控的芳香型黏合剂胶乳膜及其制备方法
CN108892755A (zh) * 2018-05-31 2018-11-27 广东基业长青节能环保实业有限公司 一种缓释型聚羧酸减水剂及其制备方法和用途
CN109628063A (zh) * 2018-12-19 2019-04-16 大连理工大学 一种聚合物改性沥青粘结剂及其制备方法
CN110272408A (zh) * 2018-03-16 2019-09-24 杭州盛弗泰新材料科技有限公司 一种光固化剂二甲基二恶戊烷醇甲基丙烯酸酯的制备方法
WO2019202038A3 (fr) * 2018-04-19 2019-12-12 University Of Tartu Synthèse et polymérisation de monométhacrylates à base d'isosorbide
KR20200052480A (ko) * 2018-11-06 2020-05-15 주식회사 제일화성 흡수성 수지용 아크릴계 가교제의 제조방법, 이로 제조된 흡수성 수지용 아크릴계 가교제 및 이를 포함하는 생분해성 고흡수성 수지
WO2020254460A1 (fr) 2019-06-21 2020-12-24 Evonik Operations Gmbh Procédé de production de mono(méth)acrylate de glycérol
CN112300306A (zh) * 2020-11-09 2021-02-02 广东石油化工学院 一种生物降解性可辐射固化的（甲基）丙烯酸酯及其制备方法
CN112566892A (zh) * 2018-08-16 2021-03-26 赢创运营有限公司 (甲基)丙烯酸酯的制备
US11414373B2 (en) 2017-01-20 2022-08-16 Evonik Operations Gmbh Glycerol (meth)acrylate carboxylic ester having a long shelf life

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WO2018031373A1 (fr) * 2016-08-12 2018-02-15 Iowa State University Research Foundation, Inc. Polyol acrylé et acylé ou acétalisé en tant que substitut d'origine biologique pour matériaux durs, rigides, thermoplastiques et thermodurcissables
WO2024105089A1 (fr) * 2022-11-15 2024-05-23 Sabic Global Technologies B.V. Composition d'asphalte à durée de vie améliorée
CN117327044A (zh) * 2023-05-31 2024-01-02 江苏集萃光敏电子材料研究所有限公司 一种超低体积收缩的丙烯酸酯类单体和应用

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